My First Time with an Older Woman

The first time I was with an older woman was a few years ago. I was 22 and she was in her mid forties. We were at a Pride after party of friend of an ex was hosting and got to talking. She had only just come out in the last year, and had an ex-husband and a teenage son.

I could tell she was really nervous as we sat in the back yard drinking and smoking cigarettes. She was telling me about how she had a new condo where she lived with her son, and how exciting her first pride was. She was also eyeing me up a lot, but really shyly and trying to act like she wasn't. I thought she was pretty cute for a middle aged lady, especially since she was small enough for me to throw over my shoulder.

As the party was winding down I decided to take a chance and invited her back to my place for a few more drinks. She stuttered a few times and blushed but she accepted. I only lived a few blocks away so we walked over, sharing another cigarette and she nervously held my hand. I opened up the front door to my building and led her downstairs to my basement apartment.

When we got inside I picked her up by her thighs and brought her head up to mine for a kiss. She was all of five feet and weighed maybe 115. I'm not huge by any means at 5'8" but I towered over her and it was fun to pick her up. She opened her mouth for my tongue, tasting of cigarettes and cheap Chardonnay as I spun her around to put her butt on the kitchen counter. We kissed like that for a few minutes as she wrapped her legs around my waist, the bottom of her dress bunching up between us.

She started panting heavily into my mouth and I pulled back from her, running my hands down her body from her shoulders, over her breasts and down to her legs, then back up under her dress. I found the crotch of her panties with one hand and ran my fingers up and down it, feeling that they were damp. I lifted her bum off the counter for a second and began to pull her panties down as she rolled her head back and stared at the ceiling through half open eyes. Her panties fell off her ankles revealing a small well trimmed bush of black hairs. I held her head back for a kiss with one hand while the other went between her legs.

I ran my fingers up and down her lips, enjoying her moans and the humping of her hips as she tried to get one of my fingers inside of her. I obliged her with first one finger then two. Her first orgasm of the night touched off when I began to circle her clit with my thumb and she squeezed her legs together so tight I thought she was trying to crush my hand. She was no longer able to concentrate on kissing me, so I left her lips and moved my head down between her thighs.

She managed to gasp "I have haven't showered yet," but I was already pressing my tongue into her. She was a little sweaty, but the taste of her arousal overpowered it. When my lips found her little clit and I pressed my tongue against it, she became incoherent, moaning and writhing against another orgasm. From what she had told me earlier that night I knew that she had never been very explorative in bed with her ex-husband, so I decided to broaden her horizons. I took one of the fingers that had been inside her and was still slick and I pressed it against her asshole. I felt her tense up for a second, but then she pushed her body down onto my finger and it slid all the way into her ass.

We stayed like that for what must have been fifteen minutes, her splayed across my kitchen counter, humping her pussy against my hand and grinding against the finger in her ass. Finally she had enough and she weekly pushed my head away, my finger coming out with a small pop as her asshole closed behind it. She was semi coherent, but she begged me to let her eat me.

I picked her up and tossed her over my shoulder, caressing and grabbing her ass as I carried her into my bedroom. I lay her down on my bed and quickly took off my boots pants and underwear. Then I climbed up on the bed, kneeled with one knee beside each of her ears and lowered myself onto her mouth. I was also pretty sweaty after being in the sun all day at the parade, but she seemed entranced by my bush and wet lips poking through the hair. She started licking, nervously at first but she quickly got into it, alternating between pushing her tongue into me and circling my clit. She obviously hadn't done it many times before, but enthusiasm made up for a lack of experience. I decided that I wanted to keep playing with her as she ate me, so I quickly turned around, settling my pussy back on her face, her nose between my ass cheeks. She got back to licking me as I pulled her dress up past her waist and over her chest, revealing a small pair of breasts covered in a black bra. I pulled the bra up as well so all of her clothes were bunched around her neck and started squeezing and playing with her breasts. She increased the pace or her licking as I started pulling on and playing with her large dark nipples.

Eventually her clumsy but enthusiastic licking set me over the edge. I sat down hard on her face, briefly smothering her as I twisted her nipples and rode out the orgasm. When I rolled off of her she was panting for breath, sweating and with a huge grin on her face. We cuddled up and almost immediately fell asleep.

When I woke up in the morning she was gone, but she had forgotten her panties and they were still in a pile on my kitchen floor.