When I was in college, I use to work at a paint store. For the most part I dealt with painters but we had the odd home owner come in from time to time. One day a middle aged woman came in and I set to work trying to figure out what she wanted as quickly as possible so I didn't have to deal with her anymore. She was pretty for a lady in her 50's and she became more flirtatious as time went on. Before too long she was putting her hand on mine, finding reasons to rub her breasts across my arm, and generally making me wildly embarrassed by her advances. After about thirty minutes of doing everything but throw me on the floor, she finally cut to the chase: "What time do you get off work? I'm going to need you to come over...and help me pick out some colors. I'll make it worth your time sweety."

So two hours later I was at her door. Before I could ring the door bell she swung open the door and gave me a kiss on the cheek and welcomed me inside, a glass of wine in her hand. Just to make double sure I knew what she was after, she was wearing a silky negligee and a robe over it that only came to her hips and was 100% see thru. Being a 20 year old guy who hadn't been laid in months, I popped a raging hard on right there in her entry way.

Being the kind hostess, she led me to her bedroom where we kissed for a few moments. "First you, then me, then you..." she whispered in my ear before she went to her knees and fished my dick out of my pants. She wasn't the best I've ever had, but she was very enthusiastic. She had some strawberry scented lube (never forget that smell) that she rubbed my balls and shaft with as she sucked away. I had to pull away a few times until a few minutes in, when I tried to pull away, she slipped her hand onto my ass, holding me close as she sucked and licked for all she was worth. Suddenly a well lubed finger slipped between my cheeks and before I could protest she slipped it in my ass. I think within five seconds of her entering me I blew a load down her throat. That was certainly not something any girl had ever done for me before and I damn near passed out.

A few minutes of kissing ensued before she laid on her bed and I started returning the favor. She made it known that she liked lube so while I was licking her clit, I spread lube all over her thighs, ass, and pussy so my hand was slick as it explored her. She was very responsive once I stuck a few fingers in her, pressing against her g-spot as I licked away. I've never had a girl tremble like that, but I've also never had a girl who insisted on me going and going and going...

Quite honestly I was starting to get bored after what must've been an hour of going down on the lady but all she kept saying was "don't stop sweety, don't stop yet" so I didn't. But I started adding fingers to her lubed and swolen pussy. First three slid in with no problem, then the fourth I had to curl under a bit but it got in too. Holy shit, I was going to fist this lady! I tucked my thumb under and slipped my whole hand in her as I lightly ran my tongure around her clit. She cried out and began grinding against my hand that had naturally folded into a fist once it got in her. I was afraid I was hurting hurt but her cries of "Oh fuck, oh fuck, oh fuck" encouraged my to keep it in her.

After a bit another orgasm rocked her and the muscles spasmed and contracted, forcing my hand back out which I immediately slipped back in, only to have it shoved back out, dripping with lube and her juices. Finally she had enough just as my hand slipped back in her. She pushed my head away from her and looked down for the first time.

"Is you whole hand in there?"

"Yes ma'm."

"Oh dear lord, I can't believe you did that."

"Is that okay? Did it hurt?"

She just smiled and said "Are you ready to fuck me yet?"

I think the concerned look on my face gave away what I was thinking; there's no way I'm going to feel anything down there tonight. She smiled and lifted her hips up and slipped a finger into her ass. "I want you in me, right here."

So, that evening I fucked her for all I was worth in her ass. I was able to put my hand in her vagina and feel my dick moving back and forth in her which was incredible. A came hard and long in her and being the sweet woman she was, she made me dinner afterwards. We fucked off and on for a year before I got it in my head that banging the older lady was holding me back from scoring with chicks my own age so I walked away from the greatest fuck buddy I could wish for.