The Dirty Old Man

Chapter 5 - Another Rendezvous With Shirley.

Before leaving for Tacoma for my two weeks with Vanessa, I bought three more butt plugs for Ellen. I'm going to take two virginities with her. I call Ellen and tell her I can't wait to see her. She says her vacation is still on but she needs to start it on September 1st. I tell her that's okay. I also tell her I want her pussy well trimmed. I want her outer labia shaved. She agrees. I check my email. There is another message from Shirley. She's got a trip to Chicago again and wants me to come up to Chicago to stay with her over the weekend on the 25th and 26th. She says she has a suite. I write back and tell her we are on.

Every two days, Vanessa and I have a video chat / masturbation session. I tell her about the date with Shirley. She says she's a little jealous. I tell her there is nothing to be jealous about, it's just recreational sex. Even Shirley calls it that and she doesn't want to get married again. I also tell Vanessa that it will be my last time with Shirley, at least without her. I tell her I'm going to invite Shirley to party with us in Tacoma.

I head for Chicago on the afternoon of August 24th. Shirley asked me to show up at the hotel at 6pm on Friday night and we'd go out to supper. I knock on her door exactly at 6pm. She kisses me and slips me the tongue. I decided not to tell her that this is the last time until Sunday night or Monday morning.

I put my things in a drawer and hang up my other clothes. We then head downstairs to the hotel restaurant. We have a great meal with some wine. After we finish eating, we head back upstairs. When we get to her suite, she pulls me inside and start stripping me. I'm standing there naked before her and she starts to lick her lips. She starts stripping for me, nice and slow. My cock is getting harder as she strips. Shirley is overweight for her height but her body is amazing. She doesn't really have rolls of fat like a lot of women have at her weight. She's just a big girl. Imagine a slim sized woman but blow up all her dimensions equally. She still has that hour glass look but with a wider middle.

When she's naked, she grabs my hard cock and pulls me over to the bed with it. She pushes me down on the bed and crawls up on top of me. She kisses me passionately and slips my cock into her pussy. She's extremely wet and ready. She lets out a loud groan as she bottoms out on my cock. I grab her breasts and begin teasing her nipples which are already hard. I pinch and squeeze them and then start sucking them. She begins to fuck me slow and easy moving up and down on my hard cock. "Oh John, I missed this. It feels so good."

We continue to fuck and I'm still sucking and tweaking her nipples. After about 5 minutes she is moving fast now and breathing heavy. I reach down between us and try to reach her clit. Because of her weight it is difficult. I eventually reach it and pinch it between two fingers. She squeals and starts to cum. I continue to pinch her clit about every 15 seconds and then start to flick it. She cums for over 2 minutes and then grabs my arm and pulls it out then she collapses onto me. I run my hands up and down her back. Eventually, she starts to breathe somewhat normally again. I raise her head and look into her eyes. She bends down and French kisses me. I look at her and say "I haven't cum yet. I want you doggie style."

She gets up slowly and gets on her hands and knees. I approach her from behind, finally putting a condom on which she didn't allow me to do before. I place the head of my cock at her pussy entrance and shove it in all the way in one stroke. She yelps and says "Oh God, John!"

I reach around and pinch her nipples again and she groans loudly. I then start moving in and out. She starts pushing back into me. We fuck doggie style for almost 10 minutes. During that time she cums twice but I manage to hold off. Eventually, I can't hold off any more so before I start to cum, I shove my thumb into her anus. This starts her off again and it's a deep cum for her. I shoot five shots of cum into the condom and pull my thumb out of her ass. She collapses and I collapse on top of her. After a minute or so, I pull out and roll over on my back. I pull the condom off and start to get up to throw it away. She say "Stop, John, I want that."

I hand it over and she turns it inside out and sticks the condom into her mouth, sucking all the cum out. She swallows it and then leans over to take my deflating cock into her mouth and cleans it off. I kiss her deeply and tell her she's awesome. We cuddle for a while and fall asleep.

Chicago, IL - August 25th.

I wake to a blowjob and at first think it's Vanessa. When fully awake I realize my mistake. Luckily, I didn't call her Vanessa so it's all good. Before I cum, Shirley says "Let's go take a shower. Bring a condom. After we wash, I'd like a good hard fuck."

"You got it, babe."

We shower and wash each other. She spends a lot of time washing my cock and it's so hard it almost hurts. She bends over, spreads her butt cheeks and says "Fuck me stud!"

I put the condom on and touch her pussy, she is soaking wet. I shove my cock into her pussy all the way in one push. "Ohhhhh!"

I begin to pound her pussy good. "Oh, yessssss, John. Do it. Fuck me hard."

I reach around and grab both her nipples and pinch them. She screams. With my left hand I reach under her and locate her clit and begin rubbing it. "Oh, God, Yessss!!"

I pound her hard for a long time and she begins to cum with "Yessssssss, John, yessssss, yesssss, Oh fuck, fuck, fuck meeeeee." I continue to fuck her and she continues to orgasm. After at least 10 minutes, I stick my right thumb into her ass and she screams and hits another orgasm peak and I start to cum. In 20 seconds, we are both pretty much done and I pull out. She pulls herself up, turns around and hugs me. She reaches down and removes the condom and eats the cum out of it. We finish the shower and dry each other off.

We lay down on the bed naked and cuddle.

She orders some breakfast from room service and when it comes we eat naked.

We spend the morning cuddling and at noon she says "John, want some lunch?"

I look between her legs and she laughs "No, actual food!"

I laugh and say "Let's go out and find a place to eat." We dress and I ask at the hotel desk about eateries. There are several very near here. We take walk and find a nice diner. The food is amazing. We walk back to the hotel after eating. We reach the room and go inside. Shirley grabs me and kisses me hard and deep. She's apparently horny again. She starts to take my clothes off. I start to remove hers.

Before long we are on the bed and at it again. She wants me to fuck her doggie style again. "John, when I start to cum, stick your finger in my ass again. That creates an awesome orgasm."

"I know that babe, I know that."

We're going at it again hard. Shirley loves hard sex. In about 10 minutes, she starts to cum again and I shove my thumb into her ass and begin moving it in and out with the same rhythm as my cock in and out of her pussy. Within seconds she's cumming hard and she starts to scream into one of the pillows. I continue to fuck her pussy with my cock and her ass with my thumb; she continues to cum as I fuck her. I last another 5 minutes and she's cumming the entire time. She finally collapses and I stop fucking her. I pull out and remove the condom. I begin caressing her. She finally starts to move and looks over at me and says "Did you cum? I didn't feel it."

"No, babe, I didn't cum but that's okay. I'll be able to cum tonight if you want to go again."

"Are you sure? I don't mind sucking you off or jacking you off."

"I'm fine Shirley, really."

She crawls over to me and lays half on me and half off. She says "Man, can you make me cum. I've never had any man that can get me off like you do."

"Why thank you sweet thing. I enjoy watching you and listening to you cum. I really do enjoy that."

She French kisses me and lays her head on my shoulder. She's asleep before I know it. I eventually fall asleep too. We sleep for a couple of hours and she wakes first and starts to kiss me and fondle my cock. I wake up and kiss her back. She's lying there playing with my penis. I smile at her "Having fun?"

She laughs and says "Yes I am."

We lie there for quite a while then I say, "It's 6:15pm, let's go to supper."

"Okay, let's take a shower first."

We climb into the shower and wash each other. She really likes washing my cock. By the time she's done, I'm hard again. "Hmmmmm," she says.

I say "Later, it's supper time. You are trying to wear this old man out, aren't you?"

"Hey, you're the one with the hard cock."

"It was fine until you spent over 5 minutes washing it. I can't help it if it likes the attention."

"Okay, later then."

We go out to eat at a restaurant we saw this noon. It has great food and we pig out. We walk back to the hotel about 8pm and decide to stop at the hotel bar. We drink three rounds of drinks and she's playing with my crotch again. We head upstairs to the room. We get to the room and start undressing each other. We jump on the bed and she jumps on me. She says "I'm going to dominate you this time."

I say "Go for it!"

She pushes me down on the bed on my back and then starts kissing me from mouth to crotch. She even sucks my nipples which I like but most women usually won't do. When she gets down to my cock, I'm hard. She spins around and puts her pussy into my mouth then goes down on me. We '69' for about 5 minutes. I'm fine but she's panting already. She gets off of me and French kisses me. She then crawls on top of me and and starts fucking me. She's pretty good too. I play with her tits which are amazing as she's pumping up and down on my cock. We fuck for over 10 minutes and she's almost there. She's sitting up so I sit up too and reach around to stick a finger in her ass. She explodes. She cumming hard. "Ohhhhhhhh, Goddddddd, Johnnnnnnn, yesssss, yessssss, Oh fuck."

I fuck her ass with my finger and she keeps cumming. She cums for over 2 minutes and then collapses on me. When she collapses my finger comes out of her butt. She lays there for a while breathing heavy. I'm caressing her.

She finally gets up and realizes I'm still hard. She get off my cock, removes the condom and starts jacking me off. About 2 minutes into it, I begin to cum and she sticks my cock head in her mouth. When I'm done, she opens her mouth and shows me my cum. Then she swallows it. She says "That's the least I should do for you since you make me cum like you do. Your cum really tastes good." Then she kisses me and we cuddle again and eventually fall asleep.

Chicago, IL - August 26th

We both sleep late today. Shirley is sucking me again when I wake up. I tell her I doubt she's going to get me to cum. She looks at me and smiles. I say "I need a bit of a rest today. I wouldn't mind eating that sweet pussy."

"Well, maybe later. I was just trying to pay you back for the number of orgasms you've been giving me."

"Girl, you don't have to. I like to give orgasms and it's not important if I get one or not....really."

"Okay." She snuggles up to me, kissing me hard.

We lie in bed cuddling and touching each other. At noon, we decide to order room service. We get up and shower together then get dressed. Lunch comes and we eat. We decide to go out for a while to do the tourist thing. We get back at around 5pm. Shirley is all over me, whispering in my ear "I'm horny, babe."

I push her down on the bed pull her shorts off and then her panties. She spreads her legs and I eat a pre-supper. Her pussy is a little tangy from all the walking and sweating. No problem. I eat the hell out of it. In about 5 minutes, she starts cumming. I continue to eat her and suck her clit. She continues to orgasm. Finally, she pushes me away from her pussy, she's had enough.

"Thanks, John, that was awesome." She kisses me and says "Wow, my juices don't taste too good, do they?"

"They're a little tangy but not bad. I enjoyed it."

"Wow, you are amazing."

"Thank you, my dear."

We shower, dress and go out to dinner. We stop on the way back at the hotel bar. We talk and touch each other and end up drinking 3 rounds. We are both a little tipsy as we walk up to the suite.

We strip our clothes off and hop into bed. She looks at me and says "John, I have a confession. I've been experimenting with anal play. I've been using some anal plugs. But I've never been fucked in the ass. I want to give you my anal virginity."

"Wow, Shirley, I'm touched. If you have been experimenting then I would be honored to break your ass in."

She breaks out the lube. I say "Let's fuck each other normally. I want you to have a couple of orgasms before we try the butt, okay?"

For her answer, she goes down on my cock and begins a very good blowjob. After a minute, I tell her to swing around and get into the '69' position. We eat each other for several minutes. I reach up and smack her on each butt cheek a couple of times. She groans with my cock in her mouth. Around the 7 minute mark, she begins to orgasm since I have been sucking her clit now for 2 minutes. She cums continuously because I am still sucking that clit. Finally, she rolls off of me and says "That's enough, I have to stop for a bit."

We lay there for a while, eventually she starts to suck me again. I'm already rock hard and ready to fuck her and take that virgin ass. I say "Shirley, get on your hands and knees." She does it. I lube her ass. It's surprisingly easily to stick my fingers into her. I get three fingers in her ass fairly easily.

I put a condom on and enter her pussy. I fuck her for several minutes in her pussy. She's moaning loudly now, building up to another orgasm. I reach under her and pinch her clit. She screams and starts to cum. I continue to fuck her and she continues to cum. I let her cum for about a minute and then pull out and begin slipping my cock into her ass. She groans loudly as I enter her ass. I'm finally balls deep in her. After thirty seconds, I begin to fuck her ass. She's groaning deep in her throat now. I'm drilling her pretty good. She says "Oh, God, John yesssss, fuck meeee."

After about 4 minutes in her ass, I can feel my orgasm building fast because she's very tight. I reach around and pull on her nipples, she says "Oh My God......" As I start to cum I pinch her clit and she joins me beginning another hard orgasm. I continue to fuck her for about 30 seconds after I cum so she can cum longer. Finally, she collapse on the bed and I slip out of her ass.

I get up and discard the condom and join her on the bed. She eventually starts to move and lays down next to me. She says "That was awesome. Thank you honey. You know, I said I was independent but I think for you, I could definitely tie the knot again."

"Well, thanks Shirley. But I need to tell you something. I'm engaged to a woman in Tacoma."

"What? How could you have sex with me if you're engaged?"

"Well, my fiance' and I have an understanding. We've actually decided to have an open marriage and we've also decided that until we're married, we can still date anyone we want. I told her about us having a weekend together."

"That is so weird. I don't see how she could have agreed to that."

"She used to be a hippy in a commune where they were always nude and always fucking anyone they wanted. Plus, she loves what I do for her. Probably reminds her of her youth. I'm madly in love with her too but I'm not jealous and it will be fine if she's with someone else. Just as long as she goes home with me."

"Well, okay. I like what you do for me too. When is your wedding?"

"Probably October 15th. She's arranging things."

"So this is probably the last time for us?"

"Yes, I don't think I'll be able to fit you in between now and early October unless you get another trip nearby. We are going to be going out with others for sexual purposes but normally it will be with other couples. Vanessa has been with other women so if you could joined us in Washington State, there would probably be some lesbian activities. You see, whoever we're with has to be with both of us. Or you'd have to have another man to join you. By the way, I'd love it if you could join us sometime, with or without a male and I'm sure Vanessa would love it too."

"I'd really like to be with you again but I'm not to sure about lesbian activity. Maybe I can talk one of the guys I work with into a foursome. I've dated him off and on for three years or so. We're off right now but he might go for it. That would be pretty cool, huh?"

"That would be super. I'd love to get into your wonderful lady parts again sometime. You are so much fun to be with."

Lying in the bed, I think how great my life has become. Two anal virginities since June. I smile to myself. I cuddle in with Shirley for awhile and we fall asleep together.

Chicago, IL - August 27th.

Early in the morning, she wakes me with a blowjob. I tell her to get into a '69' position. She swings around and we start eating each other. We go at it for 15 minutes before we both orgasm. She shows me my cum in her mouth, blows some bubbles and then she swallows it. I French kiss her and tell her she's great. I also tell her that I'm certain that Vanessa and I will welcome her with or without a male friend to a little party if she's ever in Tacoma or Seattle or even in Portland, Oregon. She says thanks and I depart her room with a long French kiss.

Illinois, August 31st

Vanessa calls. She has got the wedding set for October 15th at the Justice Of The Peace. She has also made inquiries about a larger apartment. She tells me it will be $150 extra a month plus a $500 security deposit for a large 1 bedroom but it's only $200 per month for a two bedroom. She says there are several apartments available including a two bedroom on the 5th floor on the same side as hers across from the lake. I say okay. I tell her I'm going to send her a check for $5000 and tell her to get the 5th floor 2 bedroom apartment so we can host guests. I tell her to pay the rent through the end of the year and get a mover to move her into the apartment. Also, I tell her to check the size of the master bedroom. If it will fit, buy a King-sized four poster bed with a memory foam mattress. I also tell her to buy anything she thinks we need to be comfortable in the new apartment including bedroom furniture. "Whatever you don't spend, just put it in the bank. If you need more, let me know."

She says "This is really going to happen, isn't it?"

I say "Of course, darling. I should be there by October 12th with all my things I need to get by. It won't be all that much. I am bringing my laptop, a 46" flat screen TV, a Blue Ray/DVD player and quite a few DVDs and of course all my clothes. If I need anything else, I'll buy it there or have my son send it out." I'm giving my house to my youngest son.

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Vanessa's diary: "Dear diary, August 31st. I'm happy, I'm happy, I'm happy!!! Talked to John today and he gave me a set of instructions including moving to a 2 bedroom apartment which will be our lovenest for the rest of our lives together. He's sending me a cashiers check for $5000 to get it all set up. A king-sized bed too. We'll need another dresser drawers for him. Whooohoooo!!! Mrs. John Andrews. Vanessa Andrews. Mrs. Vanessa Andrews. I love the sound of all three!!!"

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To be continued...