As the title states, 37m from SW Ohio looking for some fun with a couple for my first bisexual experience. Have not had a threesome before but it is my ultimate sexual bucket list item. Would love to chat and see if we can make something happen.
37, 5’10, 170, 6”, clean and drug free. DMs are open and would love to chat.
In my more adventurous days, as a college freshman, I was frequently searching the internet for kinky fun in my area. Not too dissimilar to today, but less action. I stumbled across a much older woman, divorced mom of two, with kids in high school. I was freshly 18 and had just started my first quarter at College and loved the idea of getting with a cougar as that had been a teenage fantasy of this horny boy.
Things started off great with the first time I walked into her townhouse and she immediately disrobed and got on her knees to take down my shorts and expose my quickly hardening cock. I had limited experience at this point, and the high school girl that I had been with was nowhere near as skilled as this mid forties milf. She took me to her bedroom and laid me down so she could continue sucking away at me and for the first time in my life she began touching my asshole. Just rubbing it while she continued to blow me with incredible eye contact. I didn’t hesitate or pull away so she kept going, eventually sliding a finger slightly into my ass which caused me to shoot a huge load of cum into the back of her throat.
We cleaned up, temporarily, and prepared for round two as I had mostly wanted to come over and feel her experienced pussy wrapped around me. We had an amazing time and yet again she made me orgasm like nothing I had felt before that time.
The next time I went to see her she again dropped to her knees in the entry way and gobbled away at my young cock. When we made it to her bedroom this time I noticed a dildo sitting on the bedside table. I asked her if she had been getting herself ready for me. “Not exactly” as a response had me puzzled. While I had watched a lot of porn at the time, this wasn’t something as mainstream almost 20 years ago as it is now.
She asked me to bend over the bed and she was going to lick my ass and play with me a little. I obliged and took my spot curled over the edge with my 18 year old ass in the air. she started off with her tongue slowly darting in and out of my anus, then came her finger, then two. She was kind and continued to check on me, making sure I was also enjoying myself which I was. Then I felt something much bigger than a finger, she told me to relax and she slowly started rubbing lube on me directly from the dildo I had noticed on the nightstand. It took a lot of slow motion and lubrication but she got it in. While it wasn’t a huge rubber cock, it was something enormous to my tight ass that hadn‘t had more than her finger in me before. She abruptly stopped and reached into the drawer for something else. I turned to watch her put on the strapon with that same dildo now attached. In my college boy slutty excitement I turned over and laid on my back instead so that I could watch her. Half to experience the visual and the other half to remind myself it was a sexy cougar pegging me. She stroked my cock while she pumped me harder and harder until I climaxed and cum shot everywhere.
We continued with similar evening excitement for several months. She had a boyfriend, who was aware of me, that lived elsewhere. At the time I wasn’t comfortable with him being involved (how I bet we all wish I had felt differently) so she started recording our experiences for him to watch later. I can only imagine what price I would pay to watch those exact tapes again. After some time we broke things off and I haven’t had any contact with her in over 15 years now. Absolutely crazy unforgettable times.