Written by Etrader
6 Feb 2017
Scarborough Fun with an older woman
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6 minute read
This story dates back to 1977 when I was only 16 years of age. My parents had taken me and my younger sister on holiday to a holiday camp near Scarborough.
Once settled in we had gone to the clubhouse where there was live music and a disco playing. I got talking to a group of lads of about 18, having told them that I was the same age. We spent a fair bit of time on the dance floor and got chatting to a group of girls whose ages ranged from about 22 up to 34. As the evening went on we retired to a corner of the bar with the girls and gradually started to pair up.
Jan, the eldest of the group seemed to take a shine to me and the thought of having sex with an "older" woman was a huge turn on for me. At the end of the evening she asked if I wanted to go back to her room with her; I said I couldn't wait! Her friend she was sharing with was going off with another guy in our crowd so she said we would have the room to ourselves.
I remember the walk back to her room as if it was only yesterday. Jan was extremely fit with a lovely pair of boobs and curves in all the right places, I couldn't wait to touch her. As soon as we got back to her room we were straight on the bed where we kissed passionately. I undid the buttons on her blouse and forcefully caressed and squeezed her tits through her bra. This seemed to turn her on as her breathing got faster and then she pushed me sideways and said enjoy what's coming next.
She stood up and slowly removed her blouse, swaying to some imaginary music, then it was her skirt. I remember thinking that Christmas had come early as I looked at this beautiful woman in front of me with matching black bra, knickers and the best of all suspenders and stockings. At 16, this was a first for me!
Jan, then climbed back on to the bed and proceeded to remove all of my clothes. My cock was absolutely rock hard and she knelt over the top of my thighs, taking it in her hand and starting to rub it. I reached up and freed her magnificent tits and started kneading them and squeezing her nipples. She moaned and took one of my hands and placed it on her pussy, needing no more encouragement I soon had one and then two fingers inside her. I fingered her for several minutes when suddenly her moaning increased and she told me to do it faster and harder. I increased the speed and put another finger inside her when suddenly she shook uncontrollably and I felt my hand get soaked by a warm fluid. Being naive, I thought she had pissed herself, but when she saw my face she quickly explained that she had squirted as she had come. To prove it she told me to lick my fingers as there would be a totally different taste. I remember thinking what the hell and proceeded to lick every bit of her juices from my hand, much to her delight.
She removed her knickers as they were soaked, but left her stockings and suspenders on, with her tits hanging out of her bra. Laying down on her back Jan said I could do anything I wanted, I climbed on top her and slid my cock into her sopping wet pussy. We fucked for a while and then she asked if I had ever had anal. I said that I hadn't and she asked if I wanted to try it. Well I was so turned on by this woman I would have done anything she asked me!
Jan said that we needed some lube and went to the bathroom where she came back with a bottle of baby oil. Laying on her back she brought her legs up and poured some oil on her fingers before inserting one and then two of them into her ass. She repeated this several times and by now my already hard cock was even harder having watched this display. Jan seemed equally turned on, her eyes had closed and she seemed be on the verge of another orgasm. I asked her if i could put some oil in her ass and she passed me the bottle, telling me to go gently at first. I poured some oil onto my fingers and for the first time ever, proceeded to insert a finger in a woman's arse. Wow, it felt great, so much tighter than a pussy and that feeling as the sphincter opened, wow.
After about five minutes Jan said she was ready. She poured some oil onto my cock and told me to push it into her ass. Still laying on her back she lifted her legs. Well, if I thought having my fingers in her ass was good, the feeling as my cock slipped into her ass was absolutely out of this world. Jan told me to start off slowly and not to push too far in, but soon she was telling me to go faster and to fill her completely, my balls were quickly bouncing off her ass cheeks.
As I pounded harder, her moans turned to shouts and then she was screaming. Her fingers were rubbing her clit really fast and she was shouting profanities at me in between her screams, I was in heaven. Jan started to shout that she was coming and I felt her ass hole tighten around my cock and then she was squirting again, there was so much fluid everywhere that the combination of this, the feeling around my cock and her screams, tipped me over the edge. I shot my load into her ass and collapsed on top of her. It was only then that we heard banging on the wall from the room next door. We both looked at each other and burst out laughing.
We laid there for some time and then Jan said she could feel my cum running out of her ass, I sat up to have a look and was amazed to see her asshole looking totally destroyed, still gaping open, red raw and leaking cum. feeling a bit worried I asked if she was alright down there and she said she'd never felt better and that was the best anal fuck she'd ever had.
This was the start of a great week's holiday where Jan taught me everything I needed to know about sex which basically set me up for the rest of my life. I owe a lot to Jan and have still got some pictures of her to remind me of that week.