When I was 19 or so I worked at an apartment building. There was a 62 year old woman that used to sit in the lobby in the mornings and wait for her bus to start running. When she would leave the lobby every morning I would watch her walk down the street till she caught her bus. At first to make sure she was safe but eventually found myself staring at her HUGE ass!
She wasn't a beauty queen, though I found out later she was a fucking KNOCKOUT as a younger woman! She was a large woman which I like. And sometimes she would use a cane when her knee bothered her. But let me tell you... She had this raw sexuality about her after we spent a few months getting to know each other 30 minutes at a time. She just started talking nasty. About how she loved sucking dick. And the sex parties she used to go to in the 70's. So being a night security guard at 19 is erection inspiring enough in this particular building and I could fill the forum with other things that happened in my 4 years there but now I'm ending my mornings with a 62 year old woman making me hard!
In hindsight she was doing everything she could to let me know we could fuck whenever I chose but I was so damn dense and I guess in awe of her age that those four years were over before I finally made my play. I eventually got in trouble for living with another women who lived in the building (I was horribly young and stupid) and we were actually breaking up at the same time I was being reassigned to another building. So I was removing some personal items from the apartment and I ran into this lady.... Lets call her Mrs. Robinson.
and she asked me why I hadn't been at the desk. I fessed up and told her the whole story and added a little twist... I told her I didn't have anywhere to stay the night.
She said I could stay with her. I follow her up to her place. She goes in the bedroom and changes into the old lady house dress number. We talked for a while and I'm still too nervous to make my move so I decide to wait and see how she going to plan out the sleeping arrangements. We had a good time. She even let me smoke weed in her place. Lol. So its getting close to 10 and she hands me towels for the shower. I hop in and do my thing. Come out and all the lights in the apt are out except her bed room. I walk in with the towel around my waist and tell her I don't have anything to sleep in but my underwear. She asks how I slept with my ex. I told her nude. She says she doesn't mind if I get comfortable. So I drop the towel and turn off the light and jump in the bed.
Obviously ROCK HARD at this point! So we just sorta cuddle. She compliments me on my penis. And then watches tv! I'm obviously gonna have to work for this a bit more. So I ask can I see her breast. She ask me if I'm a breast man (I am among other things lol) I say yes and she says how does she know if She shows them to me that I won't want more... I make my promises/lies and she pulls it out. HUGE. With the biggest nipples and areoles I had seen at that point in my life. I say I want to suck them. She laughs at me and says she knew that was coming. So I start sucking. And she starts moaning. So I start touching her all over and fingering her... She's super wet. And is cumming in a couple minutes. So I want to go down on her to really make it memorable because I know I'm not going to last long. Lol. She wouldn't let me go down her for whatever reason
So I get on top of her and slide in. So ridiculously tight. Like it hasn't been touched in ages. And I start stroking and it's like 2 minutes and I'm ready to blow. I was about to try the old position switch stall maneuver but I know the visual of that big beautiful ass won't help me hold out at all. But sure enough ms Robinson says let's to it doggy I'm better on my knees than on my back. Oddly enough the sheer fear of premature ejaculation actually got me under some control and I played it cool like... This feels so good let me do it a little longer. Lol. So I get a few more strokes in. And we go to reposition. She backs to the end of thebed and puts her ass up. My heart is in my throat it looks so damn good Audi hold of for a few more seconds the. Dive in and wrap my hands around her hips and start pumping. Thinkin ive got some control now. Well!!!..... She started fucking ME like no damn tomorrow. Ass jumping all overthe place like a damn 20 year old. And I blew it. BIG TIME!! One of those knee wobbling orgasms it takes a few minutes to recover from.
She goes in the bathroom to pee and wash and I'm laying in bed panting. She comes in the room and says... May now that that thing is drained u can get some sleep. As I'm thinking that's just what I'm about to do she says to me... We can do this as much as u want just don't hurt my feelings. I said ok and drifted off.
Morning... I wake up and she's not in the room. I find her in the living room on the computer and I walk over to her. She playing solitaire. I'm standing just beside her and she makes her move on the computer then just turns around and takes my dick in her mouth. Sucks me to full attention then makes me cum. We spent that whole morning having the best sex. So I'm leaving and I ask when can I come back. She says whenever you want. Just ring the bell. (no phone) so as I'm leaving to building the janitor who I think ratted on me for living with my ex in the first place sees me and wants to chat it up. I'm sure I had guilt written all over my face and i wasn't in the mood for him. So I went to my car and went to my moms place. 30 minute drive...Soon as I get there mom tells me my company called. I call and the operator fowards me to my ops manager (who just chewed me a new ass for living in the building ) and he says he just got a report that I was seen in the building and that I wasn't supposed to be there. I told him I was getting my belongings and that's all. He asked if I had everything and I said yes. He said if he ever heard about me in that building again he would fire me. (rat bastard janitor!!) so I never went back to see her. Couldn't call and by the time I thought to write her a letter it was such a long awkward time that I just let it go. I drive by the place often. I saw her walking into the lobby once years after but I just let it go again. I'm 32 now and to this day a lot if my masturbation ends with her on my mind