Thanks to larryinseattle for editing.
*****
A horny student's quest to fuck a MILF. His experience.
Background
The student's name is Roderick. He's good looking 21 year-old university student. He is a Dean's List student and a member of the varsity swim team. His family is very well off and until now has been a model young gentleman. He lost his virginity on his high school prom night but has not had a girlfriend since then, just the odd one-night stand.
His fraternity brother, Chuck, recently lured a MILF named Dorothy from his hometown in a frat party that degenerated into an orgy centered around her. Roderick (he doesn't like to be called Rod), missed the orgy but Chuck had shown him lewd photos that someone had taken on their cell phone. When he told Chuck that he was going to his and the MILF's hometown on some family business, Chuck told him he should call up Dorothy and threaten to release the orgy photos of her unless she has a fuck session with him. Chuck said it would work for sure. Roderick had never done anything shady but the more he thought about it when he was jerking off most nights, the more it seemed a good idea.
Here is what happened during his MILF encounter. Spoken words are in quotations but most of these are the thoughts of the young student.
Here I am waiting at the Hyatt bar in a booth at the back, not knowing whether that red haired MILF or her husband or even the police will show up. All she said was 'Yes' a few times when I called her and threatened to release her orgy photos. Maybe she had second thoughts. Fuck, my life could be ruined if I get charged with blackmail or something. But why would she risk people finding out about her indiscretion. No, I think I'm safe.
Oh, shit, I think that's her coming into the bar. I'll wave. She spotted me. Wow, she is really attractive. What a pretty yellow dress and her red hair is to die for. Better make room for her to sit beside me. I can hear the swish of her dress, of satin against satin. I wonder if she wore sexy panties like I asked. I catch a whiff of a fresh, flowery smelling perfume that is very attractive.
I can't believe that she is really here and dressed up like I demanded. This is really going to happen! I am going to fuck this beautiful woman. And this is a real woman. Not like the teen sluts at the frat house parties. I can feel my dick is getting a chubby.
"Hello, my name is Roderick and you must be Dorothy."
All she does is nod and sit there with her hands clasped together in front of her. It looks like she is pissed to be here. I don't blame her. I must admit I am a bit intimidated around older women especially beautiful women like her. What the hell do I do now?
"That's a very nice dress." Ahhh. She smiled a bit. "You remind me so much of a teacher I had in high school. She was very beautiful too." I used to masturbate frantically and think about what was under those tight skirts and white blouses. Now I'm going to find out.
Here's the waiter. "What would you folks like to drink?"
"I'll have a Seven and Seven." I look over at the pretty woman. "Please order what you want."
"A glass of white wine, whatever you have would be nice."
She has such a nice feminine voice. But what do I do if she gets bitchy and won't do what I say? That would ruin my MILF dream date.
The waiter's gone. She looks at me with pleading eyes. "Oh please, I beg you don't release those photos of me. I am so ashamed of how I acted that night. It's not like me. I should never have smoked that marijuana cigarette. Please, please. I'll do anything you ask. Just don't send those vile photos to anybody. It would ruin me.'
I can't take my eyes off her gorgeous breasts when she is talking like that. Fuck, I can't believe that I am going to be fondling those babies soon.
That's what I like to hear, some pleading. She isn't a controlling bitch like I feared. She's just a beautiful, innocent housewife that smoked pot for the first time and lost control. Well baby, you have to face the consequences. And that means fucking me.
Why don't I slide over and get a first feel of her tits. It doesn't sound like she will be stopping me after that little begging session. Here's the waiter with our drinks. Okay, now he's gone.
Hmm. I'll move real close to her. She knows I'm going to touch her but she's just sitting there with her hands together on the table. I can touch her anywhere. Hell, why not start at the breasts? Let's first check the room over the back of the booth to make sure nobody can see us. Great there are only a few people in the room and we are way in the back plus the back of the booth shields us. She could likely give me a blow job and no one would notice. Hell, not a bad idea.
Let's get a feel of her tit. God, that feels great even through the dress. I can feel her heart beating fast. She's more nervous than I am. Why don't I massage her boob a bit. I think I can even feel her nipple through the dress and bra.
"Oh Roderick you are such a naughty boy. I know you will want to unbutton my dress but when you do that, please be careful that nobody sees. I would just die of embarrassment."
Right on. I should unbutton the dress and get a good feel under that dress. There is only half a dozen buttons to open like this. I love it how she's just sitting there unmoving while I undo them. This is fun. I'm getting a woody. What a beautiful light yellow bra. I love the little lace flower trim. Here goes, I'm going to dip my hand inside that beautiful bra and get a good feel of those luscious breasts. They feel so fucking great. Her nipple is as hard as a rock. Maybe she's getting a bit turned on. Why don't I pop this titty right out of her bra. Whew, now that looks erotic.
"You have such beautiful breasts, Dorothy. Is it alright if I call you Dorothy? She nods.
