JollyJohnnyP's blog post - Fun with my neighbour - part 2 (fiction - watersports & anal)

A few days after Jenny’s revelation of her enjoyment of wetting fun and wearing men’s underwear, she popped round and asked if I was free to go for a walk. Despite the forecast being fine and the sun shining from a cloudless sky, she said it might turn out wet, so I figured that she wasn’t referring to the weather! Jenny was wearing a pink lycra top which showed off her endowment to advantage, and black soft cotton and lycra leggings, through which I could just make out that she was wearing the Jockey Midways figure hugging men’s trunks she had been wearing on “revelation day”. I decided to wear the cotton school knickers I had worn that day under a pair of black running tights, the nearest I could get to Jenny’s leggings without being blatantly feminine. It wasn’t far to the nearest park and as I had recently had plenty to drink, I was almost desperate for relief by the time we reached the park. Jenny too was showing signs of needing relief so we stopped at the first seat we came to - just a flat bench seat with neither back nor arms, which made it ideal for our requirements. I sat down and then Jenny climbed astride me but facing me with our crotches almost intimately close. She had just settled into a comfortable position when I felt a warm wetness flooding my groin, although I hadn’t yet given way to my needs. Sure enough, Jenny was relieving herself through her underpants and leggings and soaking me in the process. After checking that I still had a full bladder she led the way up a narrow path to a secluded wooded part of the park where she crouched down in front of me facing away from me, pulled the waistbands of her pants and leggings clear of her spine and asked me to use her buttock cleavage as my urinal. I was tumescent by this time but not too stiff to pee so I pulled down the fronts of my leggings and knickers and aimed at the base of Jenny’s spine before I opened the floodgates.
“Oooh, that’s lovely!” she exclaimed as she felt my hot stream hit her naked flesh and pour down between her buttocks wetting her anus on its way down to her already sopping crotch. I kept the flow going for a remarkably long time as my bladder had been near to bursting point so Jenny had an extended pleasure before the flow became a dribble then a few drops and finally stopped. We both made ourselves presentable before returning to the main path through the park and then home after a leisurely but, as predicted, wet walk. Jenny suggested we could shower together at her house so after pooping into my place for some dry clothes, I joined Jenny in her shower. The only things she removed before getting into the shower were her shoes so I did likewise and after a long warm wet hug, we stripped off, soaped, rinsed and dried ourselves before putting on dry things.
Jenny’s dry “panties” were a white jockstrap while I wore a pair of frilly pink open crotch panties. We were therefore able to participate in intimate fun without needing to undress as Jenny has expressed a strong desire to be treated as a gay man and receive my stiff cock “up my back passage” as she so coyly put it. So that’s where I put it! After her request, I rapidly became hard and with the aid of a dribble of pre-cum for lubrication, I pushed at her anus until it yielded with an “Ooooh, that feels so good” from Jenny. A regular fucking then began with Jenny clenching her sphincter from time to time as I repeatedly slid all the way in and almost all the way out. She was rhythmically pushing back in time with my thrusts and it was a beautiful sight to see my thick manhood sliding in and out of her gorgeous arsehole between two wide well rounded womanly buttocks.
All good things come to an end but I managed over twenty minutes of enjoyable thrusting before the cum came to my end in a fantastic climax as I felt spurt after spurt after spurt pulse through my cock deep into Jenny’s rectum. She didn’t want to lose my donation earlier than necessary so she put on a pair of incontinence knickers in case she leaked, before making coffee for us both. As we drank and chatted I heard a wet fart sound from inside Jenny’s knickers so I knew that she was still enjoying my gift! Before I left we agreed that we’d do it again, and again and again and again as long as we remained neighbours. I was very much in agreement with this as Jenny was the first woman I’d fucked up the arse and I’d found it very very enjoyable and it was great knowing that she felt the same way too. I returned home well satisfied and looking forward to similar activity in the future,