Judy and the Handyman 02

Jack

I get into my truck and drive away. Holy shit... what did I just do. Did I really tell this beautiful woman that I want us to be in a sexual relationship with her as a way to pay her carpentry bills? I wonder how old she is? If I had to guess I'd say late 50's. She keeps herself so well. She has all the right curves to her. She probably has no interest in a guy just starting into his late twenties. Who knows if she even has any sexual interest anymore? God I can't keep my mind from thinking about her. The more I think about her the bigger the bulge in my pants grows.

I pull into the apartment complex where I live. I check that my tool boxes are locked and head towards my apartment on the backside of the complex. The complex is nice with a pool in the courtyard for all residents to use. I cut through the courtyard and walk along the pool deck. There are 2 girls laying poolside in their skimpy bikinis. They are probably 21 or 22 each. They are hot looking but not my type.

The one girl is staring straight and the bulge in my pants. I can't conceal or control it. I have Judy controlling both of my heads! The girl staring says "You are having a battle with the bulge huh?"

The other one says "Hey handsome... I know how to fix that".... And just gives me the coy look.

I try to ignore them. The one that was staring then says "Better yet let us both fix it for you."

I say "maybe some other time." I pick up my pace and leave the girls behind.

I hear one say to the other "He is so hot... and I can't believe he just turned down a 3 way."

I get to my apartment and go in. I need a cold shower. One because it was so hot today and two because how hot Judy is. I take my boots off and strip down putting my dirty clothes in a hamper. I go to the bathroom and start the shower. I grab a washcloth and get in.

I lather up the washcloth and start at my head (the one above my shoulders) and start cleaning the dirt and grit from the day off. I wash my shoulders and chest... then wash both legs down to my feet. Finally, I wash my privates. I feel the swelling in my loins. I close my eyes and think back to Judy.

I don't even realize I have a steady stroking going as I picture her in my mind's eye. I try to picture her naked. Her soft pale skin which is so contrasting to the tan I have from working outside so much. I see her ample breasts, and her full bush. I continue pumping my fist along my shaft.

I imagine her saying Jack I want you to shoot for me.... And I feel it building.... She would encourage me telling me that it was okay, to let it go.... All the sudden I'm spurting in the shower and I'm calling out Judy... Judy as rope after rope spews out. My balls producing probably the biggest load I have ever shot. Slowly my erection fades but I'm still stroking and with my eyes closed thinking how Judy is caressing me and handling my manhood.

I open my eyes and see the ton of cum in the shower base. I get washcloth and push it down the drain. I then grab the soap and lather up my privates to clean up. I rinse and get out the shower and towel dry myself.

Later as I am pulling together dinner for myself, I wonder if I will hear from Judy. I wonder if I have scared her off??? I let out a big sigh and continue to wonder where this will go.

Judy

Oh my god what is going on? I am in a daze rethinking what Jack proposed. I say out loud "I need a drink... and a stiff one at that." Geez Judy get a hold of yourself. The stiff drink comment makes you wonder what his stiff rod is like. I can hardly remember the last time I got to see or touch one. Sheesh stiff... hard no matter what I say or think it all has innuendo. I say out loud "Judy get your trampy mind out of the gutter." I make myself a very dry vodka martini and go upstairs.

I stand in front of the mirror and wonder what does he see in me? I wonder how old he is. He looks to be around 30 but Tilly said something about being in his 20's. What does a twenty-something want with an old duck like me?

I move and look at myself closer in the mirror. I don't look bad for almost 70. I have tried to keep myself up over the years. I look at my breasts and yes there is some sag, BUT they are big and they have always served me well. I suddenly realize I didn't put a bra on today, and flashback to Jack brushing his arm on me as he passed in the hallway when he first arrived. I know my nipples were hard. I wonder if he noticed. I say "of all the days to let the girls' just hang loose I have to pick the day the hunk of a carpenter comes by."

One of the cats jumps up on the bed. I realize it has been quite some time since I shared a bed with more than a cat. I know I have it well in life. I have all the support and companionship from friends and family. I then contemplate what my family would think. They would think I lost it.

Then again what did Jack call it??? Friends with benefits? My family and friends don't need to know. "It's not like I'm getting married. As a matter of fact, that is the LAST thing I want right now."

Thinking about my sex life I realize I have often been able to separate love and sex. Sex is that physical need and desire. Sex is different when you are in love.... But it wasn't always bad when I had it with those that there was no love attached with it. And thinking back... those 20 years old can get hard again and again. Someone in their 60's has to take the blue pill wait 2 hours and then he'll yell out I'm ready. By then I have drool running down my face from sleeping, and waiting.

Hmmm what do I do? I walk over and look in my lingerie drawer. I realize I have some nice stuff to work with. I then cross the room and pull out one of my toys and climb on the bed. I wonder if I can still satisfy a man. I reach my hand down into my panties. I turn on the toy and start rubbing myself. I wonder if I can let a man penetrate me still. Do the gates even open any more? It has been a while, a real long while. What do I do???

I close my eyes and say I need an orgasm, and I wonder what Jack would think of me pleasuring myself the way I am. I fantasize about what kind of orgasm he could bring me to.

The wave builds low and comes on strong. I call out YES as it travels through me. I grab the sheets in my hand pulling them. This is one powerful O. I am panting as it continues rolling through me. GOD I scream out and feel my toes curl under. I am breathing hard. Slowly I am gaining my composure.

I'm soaking wet. I look at the sheets and it is like I am laying in a puddle. I think to myself I shouldn't have to do this alone. I get up and strip the sheets. It is while I am stripping the bedding I decide. I say out loud to no one at all. "Hell with it! I am gonna do it!"

I'm going to hire Jack on his payment terms. Worst case scenario is I fire the handyman before the work gets completed. Best case... I just grin...