This is a true story from a few years ago about my first time with Karen.
I’m a pretty keen tennis player, and have been all my life. I started attending a weekly roll-up session at my local tennis centre a few years ago with my ex, after we split up I continued going but mainly because of all the MILF’s that went, and because it was during the day time, I was the only guy under 50, which meant I was generally the focus of all their flirting. Generally we would play a set or two of men’s doubles and a set of two of mixed doubles before maybe grabbing a cup of tea before heading home.
Over the years I got to know a few of the players quite well, and would always try and get to play with the better players as much as possible. Most weeks I would end up playing mixed doubles with a woman called Karen, some weeks I would play with her and some weeks against. Karen was in her 50’s and about 15 years older than me, she was about 5 foot 5 inches, with brunette hair and very tanned skin, swimmers shoulders and a fairly flat chest but would always play in quite a short skirt that showed off her perfect legs and just gave a hint at her fantastic ass. She had the sort of body a woman half her age would kill for.
Karen was probably one of the least flirty of the women I played with, which was a shame because she was the one I fancied most. One week, just after finishing our last set of tennis, Karen approached me and asked if I wanted to play with her in the mixed tournament the following weekend. Naturally I jumped at the chance, it meant moving some things in my diary but I was willing to do that to play with this MILF. We exchanged numbers and she said she would text me with the details.
The tournament was on a Sunday, and Karen dropped me a text on the Thursday to let me know the time and offer to pick me up as I wasn’t to sure on the location and she had to drive past anyway. I agreed and Karen said she would be round at 1 o clock and to bring my ‘A’ game!
Karen pulled up outside my house where I was waiting, and I hopped in the car and we made our way to the tournament, which was about a half hour drive away. On the way we started talking and Karen told me that she was divorced for nearly 10 years and had a son who was a year older than me, although he had no interest in tennis. She enquired about my f****y and work and we made chit chat all the way to the tournament.
When we arrived at the tournament it was quickly apparent that the other players there were a bit more serious about their tennis than us and we were eliminated in the group stage, losing all three sets easily. Karen though really enjoyed herself, constantly laughing and joking, and thanked me afterwards for coming to enjoy this beating with her! As the afternoon had gone on, and we jokingly did our fist-bumps after each point and hugged each other and gave each other a kiss after each loss, things became more relaxed between us, and more flirtatious.
We started heading home about 5:30 in the evening, and as we got in the car Karen asked me if I fancied something to eat. I said absolutely, I was starving, so Karen said she had some steak at her house so I was welcome to eat there with her. I said sure, if it was not putting her out, she replied by putting her hand on my leg just above my knee, not so far as to be inappropriate but enough for me to question if she was offering more than steak!
We got back to Karen’s about 6:15, I took a seat on the sofa while Karen went and sorted some drinks, when she came back she sat down right next to me, with her leg pressed right up against mine and half leaning on me whilst taking a sip of her drink. After a minute or so, Karen started rubbing her hand up and down my leg and lent over towards me and said “Kiss me”, which I did without hesitation.
I slipped my tongue in her mouth, and put my arms around her back and started lifting up her top, revealing her sports bra, just covering a small pair of tits. I lifted up her arms and removed her bra, revealing a small but quite perky for her age pair of tits. I soon went to work on these and started licking the nipples, slowly working my way around her sweaty body, through her smooth but perfectly toned armpits and up her arm to her hand. While I was doing this, she pulled my shirt off and pushed me back into the sofa, kneeling down in front of me she yanked off my shoes and socks and then slowly pulled down my shorts and pants revealing my rock hard cock.
My cock only stand at about 5 inches, but Karen didn’t seem fussed as she took it in her mouth and sucked me off, nearly bringing me to climax but at the last second stopping, allowing me to come back from the brink. At this point Karen climbed up me and sat on top of me, she started kissing me and in between kisses said, “I’ve seen photos of you on social media, and the poses you were in with other guys I thought you were gay, that was why I never flirted with you”, I replied telling Karen I wasn’t gay, but I am extremely liberal when it comes to sex, and wanted to give her the seeing to off her life.
I flipped her over so that she was underneath me and grabbed the top of her skirt and knickers, slowly pulling them down ready to bury my face in her pussy. I started sucking on her toes whilst pulling them down and then licking all the way up her leg, removing her skirt and knickers completely whilst my tongue made its way up the inside of her thigh, out of the corner of my eye I could see glistening her pussy juice amongst a covering of pubic hair. I buried my tongue in her pussy and started eating her out, her pussy tasted perfect and was easily the wettest pussy i had ever touched. She held my head down there for a bit, but as I felt close to getting her to orgasm she pulled me up and started kissing me again, she stood up whilst still kissing me and grabbed me by the hand and led me upstairs.
We got upstairs while she told me to sit on the bed, she ran into her ensuite bathroom and shouted out, she hadn’t been with anyone since her ex-husband ten years ago, and since then had developed some fantasies she wanted to try, and she walked into the room wearing a strap-on with what looked like a 7 inch cock attached and said, you seem like the kind of guy who might enjoy this! I smiled and said I definitely was, she came over and knelt down at took my cock in her mouth again, this time spreading my legs and pushing me back and spitting on my asshole. She told me she had just lubed up the strap-on by putting it in herself before coming in and covering it in her pussy juice so it should be ok.
With this Karen held my legs back and I felt a gentle pressure against my asshole, gradually I felt the head just push its way in, Karen grabbed my hand and held it while continuing to push, my ass had taken some dick before but nothing this big. Slowly Karen pushed, occasionally stopping to ask if I was ok before I told her to carry on. When Karen had got half way in, she leaned down and started kissing me whilst giving one big thrust the rest of the way. I yelped a bit, partly in pain, partly by surprise but mostly at the thought of this hot MILF fucking me.
Karen thrusted away inside me for a minute or so, before lying back and letting me ride her for a bit. As I rode her up and down, with my cock slapping pre-cum against her on every stroke, she leaned forward and said “fuck me”. That was all the invitation I needed, as I lifted myself off her and undid the strap-on, she stayed laying on her back and I slowly entered her. Her pussy was a strange combination of exceptionally tight but really wet which made it tough to tell when I was in. I laid on top of her though and watched her eyes expand so I knew I was in, and within two strokes she grabbed me tight and started to orgasm, digging her nails into my back but not make a noise, just convulsing whilst grabbing me tighter, this was all it took for me and I simultaneously blew my load inside of her. We laid there after for about quarter of an hour afterwards, my cock stayed inside her, with our juices mixing and continuing to kiss.
Karen told me she hadn’t had a cock inside her for such a long time she felt like a virgin again, and she just couldn’t stop herself climaxing so soon and apologised. I told her not to worry, that was easily the hottest sex I had ever had, and that I did not expect to see her walk out with a strap on! We fucked again that night, and quite a few more times over the next six months or so before Karen moved away. We still keep in touch, secretly I think I’m a bit in love with her, and I love that wet pussy of hers, I can’t wait for the next time i see her!