Wife's grandpa

I'm a straight 50 yo and my wife's grandpa Leo is 75 yo widow,
Leo moved in with my wife and I a little over a year ago,
Leo and I have a good relationship we spend a lot of time together and I have noticed over the past few months that Leo has been different in a feminine kind of way,
The other day I was noticing that he was being a little flirty and he was asking me about what I thought of crossdressers and I said that I didn't know anyone who was a crossdresser but I don't think there's anything wrong with it but if that's what they want to do it doesn't bother me,
I asked Leo what brought up the subject,
He looks at me and says " I have a secret that I have not told anyone about and I don't know how to or who I can tell them,
What are you wanting to tell me about this secret of yours go ahead Leo I'm listening,
Well I hope you don't say anything about what I want to say but I can trust you,
For many years I have been secretly dressing in women's panties and I have also dressed up in lingerie and heels the works I have to confess that I love dressing up and wearing sexy nightgowns and pajamas,
So Leo and why did you tell me about your secret?
Well I guess I could trust you and I know that you would keep it between us,
Leo I think you can trust me and I want to know if you have been flirting with me for a reason for a while now and are you having some type of feelings for me?
Well I think I have a little bit of a sexual fantasy for you and I don't want you to mad at me,
No I'm not mad at you leo I am a little surprised about this but I'm okay with you telling me,
I have a question to ask you Leo " are you wearing panties as we speak and when are you going to dress up for me to see what you look like in sexy pajamas and stuff,
Leo smiling and says he is wearing panties nothing real extravagant but I have some really sexy naughty hoisery and lingerie would you like for me to put them on and show you?
Sure I would love to see you in sexy clothes,
Leo hurried to his room and a few minutes later he walked out and down to the living room,
He had put on some lace stockings and some red heels and a red and white teddy with some red panties he put on a wig and makeup,
I looked at Leo " you look like a beautiful and sexy grandma wow,
You like what I am wearing?
Yes I do I think I want to see you dressed up like that more I think you are getting me aroused,
Oh please don't say that just to be nice be honest,
Leo I am being honest with you and I am getting an erection looking at you and I am wondering if you have ever experimented sexually with a guy?
No I never have but I have masturbated a lot fantasizing about what I want to try,
What are you wanting to try if you find someone to help you with your fantasy,
I would like to have a guy a straight one to treat me like a lady and wine and dine me and after dinner get comfy on the couch put on a movie drinking some really nice cocktails,
I would sit next to him with his arm around me,
I would slowly rub his leg up to his crotch rubbing my hand on his cock as it gets really hard,
Mmmmmm sounds like it is going to be fun Leo,
As I rub my hand on your cock I would be kissing and licking your neck and I would get your hand putting it in my lingerie top asking you to squeeze my nipples,
I would unzip your pants pulling out your throbbing hard cock caressing it with both hands,
I grabbed your hand pulling it to my crotch as you put it down in my panties your fingers rubbing my soft cock you play with my balls as I get an erection,
I pull off your shirt as I get on my knees between your legs I slowly stroke your delicious cock as it throbs uncontrollably,
I put my lips on the tip of your delicious hard meat and lick it up and down I taste your delicious cock as I open my mouth as I taste and feel your meat going down towards my throat I gag as I take as much of your cock down as far as I can get it,
Mmmmmm that sounds really hot Leo and I have to admit it but I am so turned on and I think it's a good time to give it a try and see what happens,
You really want to do this with me?
Let's give it a try,
I pulled Leo up from his knees sat him on the couch with his legs on my lap,
I rubbed Leo's legs as I unbuckle his heels pulling them off I rub his foot and toes as I put them close to my mouth,
I kiss Leo's feet as I get to my knees spreading his legs open as I pull his cock out of his panties holding it in my hand I softly squeeze it as I move my head down and with the tip of my tongue I lick the head of his cock,
Leo making soft moans as I lick it up and down tasting a cock for the first time ever,
I licked his balls as I lifted his ass up I tell Leo to get on his stomach and I kiss and lick between his ass cheeks I spread them apart as I lick his butthole sticking my tongue in his hole as far as I can,
Leo is moaning telling me that ass belongs to me and I want you to be the one who devirginzes my ass and I want you to give me the ass fucking I have been longing for,
I got up as I turned Leo on his back I opened up his pajama top kissing his lips I worked my tongue down his neck and on his chest I sucked his nipples as I fingered his ass one finger at a time until I had three fingers in his ass as I stretched his butthole enough to get my cock to work it's way in his ass,
I lubed the both of us and I slowly pushed my cock in a little and kept pushing it till I was half way in,
Leo turns his head and he says "OMG It hurts a little bit but it also feels really good to!
After a few minutes of pushing it in his ass I slowly thrust in and out it feels so good I go a little faster and then I go deeper and I can feel his body shaking with pleasure as I have the same sensual feeling as his tight hole squeezes my cock,
I start pounding him fast and go deeper in his ass every thrust,
Leo moans get more loud as he screams to me and says " you have a great big cock and I love how you make my ass feel,
I'm trying to give you every inch of me in your ass to give you the best ass fuck,
As I pounded Leo's ass with everything I have leo asks if I am enjoying it as much as he does,
Yes I am enjoying it very much,
I don't want to cum yet but I'm going to pretty soon so you want me to come in your ass or what you want me to come in or on you,
I want you to come wherever you want to,
After a few minutes I was ready to blow my load,
I told Leo to turn to me when I pull out and I want you to open your mouth,
As I pulled out Leo turned around with his mouth open I couldn't wait any longer and boom I shot my load of warm man milk all over his face, mouth I put it in his mouth I could feel Leo swallow what I shot in his mouth.
He was dripping cum out of his mouth he licked as much as he was able to get,
I laid on top of Leo kissing his lips I could taste my cum,
So Leo did I give you the experience that you been wanting?
Yes you gave me more than what I was wondering what it was going to be like and more,
You like the way felt and was it a great experience for you as well?
You know what I did find it very pleasurable and I think you are sure a sexy crossdresser for you being the age you are and I am so looking forward to doing this with you more,
So am said Leo I will be wearing sexy panties and stuff everyday for you from now on and I will be ready for you anytime and anywhere you want me,

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