Category: gonewildstories

The weekend just gone brought another cosplay convention my way, and although I wasn’t able to attend every day of the event I did at least managed to make it across the country to check it out over the main weekend. That said, none of my usual friends were quite so luckily, leaving me to “fly solo” complete with my own cheap hotel room… an opportunity which has its perks, for obvious reasons.

Arriving on the Friday night, I had little more to do than find some food and then collapse onto my hotel bed, leaving me plenty of time to swipe away on Tinder until boredom and tiredness overcame me and I fell asleep. Come Saturday morning, my excitement woke me up bright and early as I had a brand-new cosplay to show off for the first time – one of my current favourite characters, Himiko Toga from My Hero Academia. The outfit was a late arrival, so I was also a little nervous as to how it would look and fit as I changed into the Japanese-style school uniform type affair, with a short dark blue skirt, oversized cardigan and knee-high black socks with simple black shoes. Finishing things off with her wig and spending some time getting my makeup right, I spent a fair amount of time pondering how I looked in the room’s mirror and making adjustments before finally deciding that I was happy. Read more »

A few years ago I was looking through craigslist and came across a post from a recently widowed older woman looking for someone to ease her back into being sexual. I sent over a pic and to my surprise got a response within a few minutes with a picture of an absolutely gorgeous woman that appeared to be late 30’s. Thinking it’s provably a pic collector I sent my number and told her if she was really interested to give me a call. Well, a few minutes later I got a call. She told me she had actually just turned 49 and her husband passed away over a year before in a car crash and she hadn’t been sexual with anyone since. She wasn’t looking for a relationship and said she didn’t want to have actual sex but did miss being romantic and sexual. We set a date and kept chatting through text for the next week until the date came. We met up for coffee one night. I was amazed at how beautiful she was. At 49 she looked better than most 35 year olds. I offered to take her for drinks but she declined because she had found drinking triggered her depression. I’m not much of a drinker anyways so I agreed coffee would be perfect. We went back to her place where she told me about her husband and their sons, how he passed and how hard it’s been without him. She started to cry but stopped herself and apologized but I told her as long as talking about it makes her feel better that I would always be a good listener. She said she really just wanted to cuddle with our clothes on and also noted that she was extremely attracted to me but my age was an issue because I wasn’t much older than her sons. I was 28 at the time. We went to her bed and cuddled for a few minutes but she was so gorgeous I had to at least try to kiss her. I held her face and started kissing her. She pulled me on top of her and we had one of the most passionate male-out sessions I’ve ever had. She said she wanted to feel my skin on hers but that sex wouldn’t be on the table. We started taking each other’s clothes off while we continued to make-out. Even though it was pretty dim I could tell she had an incredible body and I was so turned on by her. Eventually we were both naked and it was impossible to hide how turned on I was because I was as hard as I could possibly be. I started working my way down slowly waiting to see if she was comfortable and she was. I had to taste her. I started fingering her and I had to taste her. I went down on her and the first thing I noticed is how amazing her pussy tasted. She started really getting into it while I fingered her and licked her clit at the same time until she was grinding her clit on my tongue. I could have eaten her out all night but it wasn’t long until she was grabbing my head and shaking. Her pussy juice running down my arm she pulled my head up and started kissing me deep. I knew she could taste her perfect pussy on my lips and then said one of the hottest things anyone has ever said to me. “I *have* to taste your cum!”. I was so turned on at this point I stood over her as she grabbed my cock and pulled it into her mouth. She let out a sigh like she had just gotten a drink of water after being in the heat all day. She was going as deep as she could until she said “just fuck my face!”. I was quick to oblige. She was so sexy looking at me as I thrust my dick into her mouth while she never broke eye contact. I let her know I was about to cum and she took my dick all the way to the back of her throat. I could feel my balls pulsating with a giant load. She swallowed it all and we made out for a few more minutes until we both fell asleep naked. We made this a normal thing. Sometimes I would eat her out until she came and that was it. We finally did have sex up until she called me one day to tell me she met someone and thanked me for getting her back into normal life. I will always remember the beautiful widow and how amazing she tastes!