As my sex life had suddenly vanished thanks to covid, I’m going to start documenting some of my favourite experiences.
This one happened a few months ago and was my first positive experience with anal sex. Two guys previously stuck it in without consent, one was definitely taking advantage the other was an honest mistake.
I’d been hooking up with Jack for quite a few months and our sexual chemistry was A++! It was a hot summers day and I was headed to the beach when he messaged me and asked what I was up to. The beach is my happy place and I wasn’t going to skip that even for sex, so invited him along with me.
20 mins later I’d picked him up and we were on our way. I mentioned that I’d been wanting to check out an ocean pool I’d seen on social media, as we’d both never been we decided on that as our location. Little did we know this wasn’t a good idea.
We get to the pool jump in the water and swim around, flirting and talking about what we wanted to do later that day. We’d been playing around with anal play and we’re both keen to give anal a go. Unfortunately there were lots of children around so we couldn’t do much more than playful leg and arm touches. As the tension was getting high we hopped out of the water to dry off and head home.
As soon as we got out of the water he looked at his foot and had something stuck in his toe. We spoke to the lifeguards and it turns out it was sea urchin and they gave us a medical kit to remove it. For legal reasons they couldn’t help us. He turned to me and said “weirdest foreplay ever, but can you help me with this?”. After a lot of laughing about how ridiculous this situation was, groans of pain on his part and repeated sorries on mine I got it (minus are tiny little shard) out and we headed back home.
This was an absolute mood killer and I offered to drive him home whilst being really disappointed of how our cute little date had played out. He was equal parts concerned about his health and also horny and wanting to relieve the sexual tension between us. On the drive back to our neighborhood he decided he was too horny and his foot can wait. So we went back to my house, with a quick detour for some medical supplies and beer.
Being the considerate person I am cleaned his foot with vinegar and put a band aid on his foot and kissed him on the forehead before we hopped in the shower to clean the salt water off ourselves. In the shower we finally got to make out properly and explore each other’s bodies. We fondled each other and made out for a while then moved back to the bedroom. He pushed me down on the bed then started to kiss me all over going lower and lower until he was eating my pussy. He’s good at so it doesn’t take long until I’m moving my hips, grabbing his hair and coming hard.
I usually repay the favour but he really wanted to fuck so started fucking me missionary as we made out. It was hot and intimate but we did say we want to to explore anal more so he flipped me over and stretching me out with lube and his fingers before sliding my plug in. He started fucking me doggy style whilst my plug stretched me and I was in heaven. I was moaning and so into it and wanted more so I asked him to fuck me in the ass. He didn’t need telling twice and he swapped my plug with his dick immediately going slow at first whilst I got used to him. Thankfully there was no pain and it actually felt amazing. I was so full and loving it. He then pulled out and rolled me onto my back so he could make eye contact as he fucked my ass. He got more primal and I reached down to play with my clit and rubbed it til I came for a second time. I’m fairly sure my orgasm pushed him over the edge because he came almost immediately after me. We collapsed in a sweaty mess and cuddled for a little bit before we came back to reality.
The non sexy end of the story was that is friend who’s a nurse couldn’t get the rest of the barb out so he needed to go to ER and get it cut out. We didn’t realise it was that serious, but as he’s completely fine and lived to tell the tale we’ve laughed about it every time we’ve seen each other since. Definitely the most eventful/weirdest prelude to sex I’ve ever had.
Source: reddit.com/r/gonewildstories/comments/g0hlbu/mf_a_series_of_misfortunate_events_lead_to_anal