Memories of a 50 yr old man | 2016

Sigh... thinking back to one of my first times.... It may sound like a dear penthouse letter, but it isn't....

I was just 18, birthday in April. She was 38. We met as we were volunteers with a sporting event happening in our city that summer. The first second I met her at orientation, I was aw struck. Fuck, she was gorgeous and this young lad was showing it in his face and actions and voice. ...

We chatted a little general chit chat during break.... but there were guys lined up to chat with her all evening long.

Well, lucky me one day during the event, we had to work with each other... All shift long we chatted and I think she chatted more with me because I think she thought I wouldn't put a move on her, or at least I wasn't in her league so she thought it was safe to be more open. I was trying and trying to hit on her and ask her out... but lacking confidence and experience, I didn't know what was happening....

We worked late one night and as it was after midnight and the local busses had stopped running in her neighbourhood, I offered her a ride home as did the ten other fella's in the section. She picked me, as I was the safer bet, I guess. Dropped her off at home (sweet, I knew where she lived!) She asked if I wanted a drink of water or something... Nah, I'm fine, it's late, gotta work in the morning... See you tomorrow.... What an idiot I was.. I didn't even catch the head tilt and sly smile... Wait for her to get in the house and off I drove.

Towards the end of the events, the small section we worked in had a volunteer BBQ. Well at the BBQ, she must have had a few drinks and gotten tired of being hit on! She comes up to me and says, lets go and grabs my hand and drags me outside away from the crowd. Out to my car and she waits patiently for me to open it... in we go and boom, she grabs me and kisses me. "God Fred (not real name), I've been wanting to do that since you drove me home that night" I ulpped and stuttered.. What? God I've been horny for you since day one. We sit in the car and talk and talk and occasionally kiss and hold hands. Seems she likes the young lads and here I am a young lad not knowing anything about cougars or lynx's or bobcats or what ever a hot older lady was called. I just knew, what the F and was I going to see her naked!?!?! I drove her home later that night and she said "Yes, we can go out on a date next week. Pick me up at x hour on x day" Awesome.... I meet her on x day at x hour and off we go shopping... We head to a local lingerie shop and she says pick out something you think is sexy for her to wear and she'll pick out something that she thinks is sexy.... My choice was a lousy choice... again, lack of experience.. She picks out a very nice sheer nightgown with matching lace panties... We get the goods and spend the rest of the afternoon together. Going here and there, seeing this and that.. and all the time, I just want to see her in that outfit and fuck her.....

Well, after dinner and a nice restaurant, we finally head back to her place... Saweet! Once we get in the door, we kiss and I'm instantly hard. My hands are going a mile a minute and kissing like an idiot... She sits me down on the couch and pulls out my cock and gives it a few good strokes and goes down on it aaannnndddd He's done!! Aw crap... I'm sorry... Shit I wanted to last...

No worries she says... She did that on purpose.. to make me last longer... Next time we go out.. jerk off before I come to get her, I will last longer later....Check.

She excuses herself to go and change... As she leaves, she says, get undressed. totally naked and wait here.

She comes back in that wonderful nightgown and panties with two glasses of wine.. and of course the young man I am, I'm f'n hard again just seeing her like that... and being a little shy, of course I'm covering my cock...

She sits and hands me the wine.. I sip nervously..

We kiss and talk and my hands roam... mmm, caressing her tits through this sheer top.. oh my, how good her nipples look through it... and I can touch them all I want....

She get up and leads me to the bedroom... Holy f, her ass looks gorgeous in that sheer gown... I just stumble along behind her,, cock pointing right at her ass.... aching to be thrust into her....

Once in the bedroom, she lays on the bed and taps the bed right beside her inviting me to lie down... She grabs the flagpole and caresses it... as we kiss.. my hand explore her body... tugging the gown up to touch her pussy...

Her top comes down and there I am, a baby sucking on her beautiful tits.. Oh man... they are so wonderful... Not huge, not small... a very nice c cup, I learned later... Nice small pink areolas and very erect nipples... mmmmmm... so wonderful to suck and hold...

As she gets up on her knees to go lower on me... she scoots her ass up towards my face and leads my hand up to caress her ass... mm,, it feels so good.. Lift up the gown and touch her butt .. I start tracing the outline of the panties down to her pussy.. oh my, she's getting very wet... as I touch her cootch... she wiggles her ass and moans on my cock... and her moaning on my cock makes it jump a little in her mouth and she moans a little more.. and I touch her cootch a little more.. eventually her panties are to the side and I'm fingering her very wet very tight pussy.... I've got one... then two.... then three fingers in her pussy as she's blowing me... occasionally stopping blowing me to breathe and whisper fuckkkkkk... yeeesssss, keep going... finger fuck me... FINGER FUCK ME!!!! YESSSSSSSS mpmpmppjjphjhhhphphphmm

After she comes on my fingers, she kneels up and takes off the gown and then rolls on her back and off come the panties... Never really did see them on her except through the night gown... but fuck they did look nice that way too....

She pushes me back down on the bed, grabs my cock and climbs on it... Teasing her clit a little with the head... teasing me by rubbing in on her clit.. She sits right down on the shaft of my cock and rides my dick, sliding herself back and forth on it.. stimulating her clit even more... I can feel the warmth of her cunt on my balls...

She must of had a small orgasm as she slows down a little and finally lowers herself onto my hard hard cock.... Oh god,, she is so fucking hot in there... concentrate... looking up at her.. she is in heaven... a beautiful tight body, nice firm tits.... riding my cock... She leans a little to one side and caresses her breast and pulls the nipple.. she leans down and holds her tit and offers it to my mouth.. my tongue and her finger play with her nipple.. as she grinds away on my cock......

She leans back and reaches behind and grabs my ankles as she grinds hard on my dick, moaning,,, yes yes yes... mmmm... yes...

I about to blow my load and start tensing up and she stops and gets off...What,, where'd she go... wtf..... Relax a little .. don't come too soon...

I take a small breather and get a drink of water... I come back to the bed and she's on her knees... Hmm, never done that position before... I get in behind her and start to line up the cock for her cunt and she wiggles her ass, saying that I need to slap it first before I can put it in... I tap it.. she wiggles and says slap it.. not tap it.. I slap it and flinches a little.. better... but slap it... slap it... Ok,,, I slap it and she flinches more.. yes.. again.. One more time with feeling and she thrusts back on to me ....

Oh god.. her cunt is so warm.. and she's fucking me as I'm behind her... holy F!!! After a few minutes of this.. I lean over her back and reach around to play with her tits and nipples.. reach down lower and play with her clit and feel my cock going in and out of her pussy.. Holy FUCK>>>>I'm gonna cum...

It's ok she yells... do it on my back... Mph mph... I pull out after one pump in her pussy and hold my cock against her butt hole and spurt a few good shots on her back... first time for that too...

Holy fuck.. I'm spent... I sit on the edge of the bed as she gets up and heads to the bathroom to clean up a little.... I'm laying back on the edge of the bed when she comes back and places a small kiss on the shaft of my cock and says thank you....

I pull her up and kiss her deeply and caressing her... we climb into bed and I snuggle in behind her to spoon her in the after glow..... ahhh...

And yes, we did it again in the middle of the night and she made breakfast in the morning....and we did it in the kitchen too....